JP2014508184A5 - - Google Patents

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Publication number: JP2014508184A5
Authority: JP; Japan
Prior art keywords: phenyl; substituted; cycloalkyl; alkyl; heterocyclyl
Prior art date: 2012-03-16
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP2013558454A

Other languages

English (en)

Japanese (ja)

Other versions

JP6050264B2 (ja

JP2014508184A (ja

Filing date

2012-03-16

Publication date

2015-05-07

2012-03-16 Application filed filed Critical

2012-03-16 Priority claimed from PCT/EP2012/054631 external-priority patent/WO2012123563A1/en

2014-04-03 Publication of JP2014508184A publication Critical patent/JP2014508184A/ja

2015-05-07 Publication of JP2014508184A5 publication Critical patent/JP2014508184A5/ja

2016-12-21 Application granted granted Critical

2016-12-21 Publication of JP6050264B2 publication Critical patent/JP6050264B2/ja

Status Active legal-status Critical Current

2032-03-16 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
150000001875 compounds Chemical class 0.000 claims 21
125000000623 heterocyclic group Chemical group 0.000 claims 15
125000000753 cycloalkyl group Chemical group 0.000 claims 10
229910052736 halogen Inorganic materials 0.000 claims 10
150000002367 halogens Chemical class 0.000 claims 10
-1 cyano, hydroxyl Chemical group 0.000 claims 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
239000003112 inhibitor Substances 0.000 claims 7
239000008194 pharmaceutical composition Substances 0.000 claims 6
125000001072 heteroaryl group Chemical group 0.000 claims 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
229910052731 fluorine Inorganic materials 0.000 claims 4
239000011737 fluorine Substances 0.000 claims 4
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
239000003795 chemical substances by application Substances 0.000 claims 3
201000010099 disease Diseases 0.000 claims 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 2
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 2
102000012440 Acetylcholinesterase Human genes 0.000 claims 2
108010022752 Acetylcholinesterase Proteins 0.000 claims 2
206010019375 Helicobacter infections Diseases 0.000 claims 2
206010028980 Neoplasm Diseases 0.000 claims 2
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 2
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 2
229940022698 acetylcholinesterase Drugs 0.000 claims 2
LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims 2
125000003302 alkenyloxy group Chemical group 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
125000005133 alkynyloxy group Chemical group 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
230000001771 impaired effect Effects 0.000 claims 2
230000002757 inflammatory effect Effects 0.000 claims 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
238000000034 method Methods 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
201000006417 multiple sclerosis Diseases 0.000 claims 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
239000012453 solvate Substances 0.000 claims 2
125000004001 thioalkyl group Chemical group 0.000 claims 2
NITUEMISTORFON-PPFXTMJRSA-N (2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2R)-2-aminopropanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]-3-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@@H](C)N)C(C)C)C(C)C)C1=CC=CC=C1 NITUEMISTORFON-PPFXTMJRSA-N 0.000 claims 1
208000023697 ABri amyloidosis Diseases 0.000 claims 1
208000017227 ADan amyloidosis Diseases 0.000 claims 1
208000024827 Alzheimer disease Diseases 0.000 claims 1
102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
102000009091 Amyloidogenic Proteins Human genes 0.000 claims 1
108010048112 Amyloidogenic Proteins Proteins 0.000 claims 1
201000001320 Atherosclerosis Diseases 0.000 claims 1
208000012639 Balance disease Diseases 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
206010009944 Colon cancer Diseases 0.000 claims 1
208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
201000010374 Down Syndrome Diseases 0.000 claims 1
206010061825 Duodenal neoplasm Diseases 0.000 claims 1
208000030814 Eating disease Diseases 0.000 claims 1
208000019454 Feeding and Eating disease Diseases 0.000 claims 1
229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims 1
208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
208000023105 Huntington disease Diseases 0.000 claims 1
201000000162 ITM2B-related cerebral amyloid angiopathy 1 Diseases 0.000 claims 1
201000000194 ITM2B-related cerebral amyloid angiopathy 2 Diseases 0.000 claims 1
101710144961 Interferon tau-1 Proteins 0.000 claims 1
101710144950 Interferon tau-2 Proteins 0.000 claims 1
101710144962 Interferon tau-3 Proteins 0.000 claims 1
102000004388 Interleukin-4 Human genes 0.000 claims 1
108090000978 Interleukin-4 Proteins 0.000 claims 1
208000027747 Kennedy disease Diseases 0.000 claims 1
206010027476 Metastases Diseases 0.000 claims 1
206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
229940082332 Muscarinic M1 receptor antagonist Drugs 0.000 claims 1
108010008881 NBI 5788 Proteins 0.000 claims 1
229940127523 NMDA Receptor Antagonists Drugs 0.000 claims 1
229930012538 Paclitaxel Natural products 0.000 claims 1
206010033645 Pancreatitis Diseases 0.000 claims 1
102100031674 Protein-L-isoaspartate(D-aspartate) O-methyltransferase Human genes 0.000 claims 1
201000004681 Psoriasis Diseases 0.000 claims 1
208000028017 Psychotic disease Diseases 0.000 claims 1
206010037779 Radiculopathy Diseases 0.000 claims 1
102100028656 Sigma non-opioid intracellular receptor 1 Human genes 0.000 claims 1
101710104750 Sigma non-opioid intracellular receptor 1 Proteins 0.000 claims 1
206010054184 Small intestine carcinoma Diseases 0.000 claims 1
208000005718 Stomach Neoplasms Diseases 0.000 claims 1
208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 claims 1
201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims 1
229960002916 adapalene Drugs 0.000 claims 1
229960000548 alemtuzumab Drugs 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
229940035678 anti-parkinson drug Drugs 0.000 claims 1
239000000935 antidepressant agent Substances 0.000 claims 1
229940005513 antidepressants Drugs 0.000 claims 1
239000000164 antipsychotic agent Substances 0.000 claims 1
229940005529 antipsychotics Drugs 0.000 claims 1
239000002249 anxiolytic agent Substances 0.000 claims 1
230000000949 anxiolytic effect Effects 0.000 claims 1
229940005530 anxiolytics Drugs 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
210000000467 autonomic pathway Anatomy 0.000 claims 1
239000002439 beta secretase inhibitor Substances 0.000 claims 1
230000033228 biological regulation Effects 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
208000035269 cancer or benign tumor Diseases 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
208000010877 cognitive disease Diseases 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
230000003210 demyelinating effect Effects 0.000 claims 1
230000008021 deposition Effects 0.000 claims 1
238000010511 deprotection reaction Methods 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
235000014632 disordered eating Nutrition 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
201000000312 duodenum cancer Diseases 0.000 claims 1
230000004064 dysfunction Effects 0.000 claims 1
230000008482 dysregulation Effects 0.000 claims 1
230000037149 energy metabolism Effects 0.000 claims 1
239000003623 enhancer Substances 0.000 claims 1
239000002792 enkephalinase inhibitor Substances 0.000 claims 1
239000002532 enzyme inhibitor Substances 0.000 claims 1
229940125532 enzyme inhibitor Drugs 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000012530 fluid Substances 0.000 claims 1
239000003540 gamma secretase inhibitor Substances 0.000 claims 1
206010017758 gastric cancer Diseases 0.000 claims 1
201000000052 gastrinoma Diseases 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
239000003395 histamine H3 receptor antagonist Substances 0.000 claims 1
230000013632 homeostatic process Effects 0.000 claims 1
230000003054 hormonal effect Effects 0.000 claims 1
230000028996 humoral immune response Effects 0.000 claims 1
239000002955 immunomodulating agent Substances 0.000 claims 1
229940121354 immunomodulator Drugs 0.000 claims 1
229960003444 immunosuppressant agent Drugs 0.000 claims 1
239000003018 immunosuppressive agent Substances 0.000 claims 1
208000000509 infertility Diseases 0.000 claims 1
230000036512 infertility Effects 0.000 claims 1
231100000535 infertility Toxicity 0.000 claims 1
108700027921 interferon tau Proteins 0.000 claims 1
229940028885 interleukin-4 Drugs 0.000 claims 1
230000023404 leukocyte cell-cell adhesion Effects 0.000 claims 1
230000021633 leukocyte mediated immunity Effects 0.000 claims 1
230000003211 malignant effect Effects 0.000 claims 1
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 claims 1
239000003771 matrix metalloproteinase inhibitor Substances 0.000 claims 1
201000001441 melanoma Diseases 0.000 claims 1
230000009401 metastasis Effects 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
230000005012 migration Effects 0.000 claims 1
238000013508 migration Methods 0.000 claims 1
208000027061 mild cognitive impairment Diseases 0.000 claims 1
125000002757 morpholinyl group Chemical group 0.000 claims 1
239000000234 muscarinic M1 receptor antagonist Substances 0.000 claims 1
229960005027 natalizumab Drugs 0.000 claims 1
230000004770 neurodegeneration Effects 0.000 claims 1
239000004090 neuroprotective agent Substances 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
229960001592 paclitaxel Drugs 0.000 claims 1
230000001717 pathogenic effect Effects 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
208000037803 restenosis Diseases 0.000 claims 1
206010039073 rheumatoid arthritis Diseases 0.000 claims 1
201000000980 schizophrenia Diseases 0.000 claims 1
208000020685 sleep-wake disease Diseases 0.000 claims 1
201000011549 stomach cancer Diseases 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
108010018276 trimethylguanosine synthase Proteins 0.000 claims 1
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims 1
239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims 1

JP2013558454A 2011-03-16 2012-03-16 グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 Active JP6050264B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201161453333P	2011-03-16	2011-03-16
US61/453,333		2011-03-16
PCT/EP2012/054631 WO2012123563A1 (en)	2011-03-16	2012-03-16	Benz imidazole derivatives as inhibitors of glutaminyl cyclase

Publications (3)

Publication Number	Publication Date
JP2014508184A JP2014508184A (ja)	2014-04-03
JP2014508184A5 true JP2014508184A5 (2)	2015-05-07
JP6050264B2 JP6050264B2 (ja)	2016-12-21

Family

ID=45852540

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2013558454A Active JP6050264B2 (ja)	2011-03-16	2012-03-16	グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体

Country Status (6)

Country	Link
US (1)	US8530670B2 (2)
EP (1)	EP2686313B1 (2)
JP (1)	JP6050264B2 (2)
DK (1)	DK2686313T3 (2)
ES (1)	ES2570167T3 (2)
WO (1)	WO2012123563A1 (2)

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DE102015011780A1 (de) *	2015-09-16	2017-03-16	Hochschule Anhalt	Neue Glutaminylcyclase-lnhibitoren
AU2018208458B2 (en) *	2017-01-10	2020-07-16	ETH Zürich	Cell-protective compounds and their use
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EP3543231A1 (en) *	2018-03-19	2019-09-25	ETH Zurich	Compounds for treating cns- and neurodegenerative diseases
CN108611370A (zh) *	2018-05-10	2018-10-02	江苏天瑞精准医疗科技有限公司	一种pimt表达质粒、扩增引物、构建方法及应用
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KR20240024948A (ko) *	2021-06-24	2024-02-26	인실리코 메디신 아이피 리미티드	질환의 치료를 위한 베타-락탐 유도체

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